Dimethylcarbamoyl Chloride → Trans-3-(4-chlorophenoxy)-4-hydroxy-N,N-dimethyl-1-pyrrolidinecarboxamide

HRID 1381220Notes

Reaction equation

HRID 1381220 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH:7]2[CH2:11][NH:10][CH2:9][CH:8]2[OH:12])=[CH:4][CH:3]=1.[CH3:15][N:16]([CH3:20])[C:17](Cl)=[O:18].C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][C@H:7]2[C@H:8]([OH:12])[CH2:9][N:10]([C:17]([N:16]([CH3:20])[CH3:15])=[O:18])[CH2:11]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 13320209HCID 13320209, compound

Product 1

HCID 13320214Trans-3-(4-chlorophenoxy)-4-hydroxy-N,N-dimethyl-1-pyrrolidinecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3.5 g. of 4-(4-chlorophenoxy)-3-pyrrolidinol, 1.8 g. of dimethylcarbamyl chloride and 1.7 g. of triethylamine in 300 ml of methylene chloride was stirred for 60 hr. The solvent was removed under vacuum, 300 ml of benezene was added and the mixture was refluxed for 2 hr., then filtered. After solvent evaporation, the residue was dissolved in cyclohexane-benzene and charcoaled. The product was then crystallized, collected by filtration and recrystallized from cyclohexane-benzene; m.p. 137°-142° C.

Workup

  1. customThe solvent was removed under vacuum, 300 ml of benezene
  2. additionwas added
  3. temperaturethe mixture was refluxed for 2 hr
  4. filtration, then filtered
  5. customAfter solvent evaporation
  6. dissolutionthe residue was dissolved in cyclohexane-benzene
  7. customThe product was then crystallized
  8. filtrationcollected by filtration
  9. customrecrystallized from cyclohexane-benzene

Sources & evidence

ORD record
ord-a1800dec433e46b2aff70c16bb67f4c6
Source dataset
uspto-grants-1986_04
Patent number
US04585785

Reaction notes

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